


Fluff/Angst Prompts- Oswald Cobblepot

by JokesterWrites



Category: Gotham (TV)
Genre: F/M, Reader inserts, Tumblr Prompts
Language: English
Status: Completed
Published: 2016-10-13
Updated: 2016-10-13
Packaged: 2018-08-22 06:35:37
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 4,658
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8276221
Author URL: https://archiveofourown.org/users/JokesterWrites/pseuds/JokesterWrites
Summary: Upload from my Tumblr collection of one shot fics regarding Oswald Cobblepot.Each chapter is a stand alone one shot.





	1. Chapter 1

Oswald stepped into the foyer of his house. “Darling, I’m home.” He announced, hanging up his jacket and bowler hat on the coat rack, and tossing his umbrella into the holder by the door.

He could hear giggles coming from upstairs and he smiled to himself. Must be bathtime, he mused, following the sound of the joyful shrieks of his young son. Reaching the top of the stairs he started down the hallway, until a small blur flew past him. Oswald reeled back out of the way as you followed the small blur.

“Come back here my little Penguin.” You laughed chasing your son son the hallway. Oswald frowned in confusion, “Penguin.” he questioned curiously. You paused to kiss Oswald on the cheek. “I’ve got an escapee.” You explained glancing over the onesie clad scamp. The little troublemaker in question slipped and scampered into your bedroom, crawling onto the king sized bed and jumping up and down gleefully in his new Penguin onesie. “Honk Honk, mama!” He waved his arms around. “I’m a penguin! Like daddy!”

You chuckled at him. He did look rather like his father. All dark spikey hair and big blue eyes. You collected him into your arms, and kissed the top of his still damp hair. “What an excellent Penguin you are, Benjamin.”

Oswald paused in the doorway to watch the pair of you. He had never felt more blessed than in these moments together. “Daddy!” Benjamin had caught sight of his father and squirmed in your arms. Oswald grinned, “Come here my little Cobblepot.” He bent down, arms open to receiving his son. “How was bathtime?”

“I am a Penguin. Honk Honk!!” Benjamin waved his flipped encased arms. Oswald chuckled, “Honk Honk is what geese say, silly.”

His son pouted before a yawn took over him, “But mum said that’s what you say.” Oswald raised an eyebrow at you. You winked in response. “I think it’s time for bed though. This little Penguin looks tired.” You kissed both of your boy’s cheeks. Benjamin beaming sleepily at his mother’s love, while Oswald smirked. “Off to sleep. You’ve got a big day tomorrow. We’re going to the zoo.”

“I’ll put him to sleep.” Oswald offered. He tucked Benjamin in and told him a story until his eyes closed and breathing slowed when he drifted off to sleep. You watched quietly with a soft smile from the doorway, unwilling to interrupt this precious moment. Oswald turned on the nightlite and carefully closed the door behind him. “Have I told you I love you today?” You whispered when he wrapped his arms around you.

Oswald hummed thoughtfully, “I don’t think so.” he teased you. He lead you down the stairs to the living room where he turned on the old gramophone. The gentle tap of the piano played out ‘Can’t Help Falling in Love with You.” Oswald carefully drew you into his arms and together you gently rocked back and forth. “Well I love you so very much.” You leaned your head against his shoulder, closing your eyes as you swayed.

Oswald tilted his head to kiss the top of your hair. “I love you too. You’ve brought me so much happiness.” He whispered, afraid to break the serene moment. The room fell into sweet silence as you enjoyed the simple pleasure of a dance.


	2. Marry Me (proposal)

How beautiful to find a heart that loves you without asking for you for anything, but to be okay. 

When Oswald realized this about you, he immediately knew he had to ask you to marry him. Meticulous planning with Gabe had made him nervous, but he wanted everything to be perfect. His nerves were simply a sign that it was the perfect decision.

Oswald took you out to the docks along Gotham’s canal. It was an odd place to propose he mused, but this exact pier where he was taking you was where everything for him had truly started. He’d ‘died’ here and been reborn here in many ways. Tonight was hopefully another new beginning for him.

It was early evening and the sun was just beginning to set, casting golden colour over the water. Gabe had arranged for a candles to light your way and a lover’s bench to be ready at the very end of the pier. You beamed in wonder at how lovely everything looked. Oswald was always so thoughtful. He lavished attention on you and often tried to shower you with extravagant gifts. No matter how often you reminded him that you didn’t need material proof of his affection, he still tried. Eventually you had to make a compromise. He could only only bestow gifts in the form of experiences with him. Since then he’d insisted on grand dinners and events to exploit the loophole of buying you new clothes and jewelry for the event. In fact, he’d gifted a new dark purple dress on you with a fur trimmed coat just for this occasion.

“Oswald, it’s beautiful.” You sighed happily, leaning into him to watch the sunset over the water.

Oswald smiled, “It’s nothing compared to you, my dear.” He loved making that blush run across your cheeks. “I have something I’d like to ask you.” His voice quivered with nerves. Suddenly the collar of his shirt felt too tight, and the cravat too restraining.

Especially when you looked at him with those big innocent eyes framed with dark lashes. He could hear his heart hammering in his chest. He prayed you couldn’t tell how nervous he was.

“Anything… Oswald are you alright?” You asked concerned, placing a hand on his arm when he looked like he was going to choke on his words.

“Fine.. perfectly fine.” He recovered a little, “Um.. isn’t that a lovely boat?”

Confused, you glanced over to where he was gesturing. It was an old fisherman’s boat. Nothing particularly special. “Oswald I don’t under-” When you looked back at him your heart stopped.

He had taken the opportunity of your distraction to get down on one knee. “I couldn’t imagine anyone more perfect to spend the rest of my life with. Would you do me the honour of marrying me?” He fumbled with the ring box, and you hand instantly went to your mouth and you nodded, tears beginning to form in your eyes. He carefully placed the ring on your finger with a silly wide grin on his face. You didn’t even glance at the ring, but instead threw yourself into his arms. Oswald toppled over with you and you kissed him senseless.


	3. Misunderstandings (love letters gone wrong)

It was with trembling fingers that you carefully placed the cream coloured envelope on the tea tray. With any luck it would be the first thing Oswald saw this morning. No longer able to keep your ardent feeling for him to yourself, you had summed them up the best you could on paper. It would perhaps be much easier than facing your fears of rejection and disdain by telling him in person. At least this way you both could pretend he hadn’t seen it if your feelings were not returned.

Hurrying out of his study, you busied yourself about the mansion, fretting as you waited for Oswald to rise for the day. He was not typically an early riser, preferring to take tea in his study around mid morning. Then you heard the unique sound of his step echoing through the hallway.

“Good morning,” Oswald greeted cordially, and motioned for you to follow him. “What’s on my schedule today?” He questioned, taking a seat and pulling the tray towards him. Pausing over the croissant, Oswald’s interest was peaked by the envelope with his name on it. Turning the weighted paper over in his hands, he broke it open, pulling the pages from inside.

Suddenly your mouth was dry and the feeling of anxious butterflies permeated your stomach. His face was unreadable as his eyes speed over the words.

“My dearest Oswald,

I’m afraid I can no longer hold my tongue. My feelings for you have become to great to ignore every day. Ever since that first glance at you, my life shifted as a whole, because in an instant I understood what love really is, because I understood that when love and joy are shared, move intense they become, and that grief and hardship are a lesser burden when faced with clarity and trust.As much as I make myself beautiful, when I approach you I feel like an “ugly duckling” next to a fascinating, natty, elegant swan.

Your voice is sensual, your gestures are elegant, and your good taste for with your clothes also impresses me, although you have a casual way about you. I love your way of being discrete (for example your shy, but sincere, smiles). Your soft-spoken and paused talk, and your intelligent and relevant remarks…..”

Oswald did not bother to finish the letter properly. He recognised your elegant handwriting. Hurt and anger swelled through him. This was a cruel joke. A poorly played and very unappreciated joke. You must know of his feelings towards you, how desperately he wished that you would be his. But he knew his own image, how you saw him as some elegant… swan…. was proof of how ridiculous this whole letter was.

Jaw tightening, he ripped the letter to pieces right in front of you. “How very… amusing.” Oswald snarled, his face hard and angry as he tossing the remnants into the fireplace. They would burn later. That’s when he heard it.

A sob.

Oswald turned to you, confused and bewildered at the hurt swimming in your eyes. Those beautiful hands that he longed to touch were placed over your mouth, stifling the cries that shook through your body. Then the first tear spilled down your face, and Oswald was suddenly very much aware that this had not been a joke. You had been sincere in your words and he had destroyed them. You turned and ran out of the study.

“Wait!” Oswald was not far behind, wanting to correct the error of his judgment. He caught your wrist and tugged you back into him. The grip around your arms tightened as you struggled to remove yourself. However you weakened at Oswald’s desperate gaze, how his apologies spilled over his lips. “I’m so sorry. I didn’t know! I just… I love you, and it’s hard to believe someone as wonderful, and as smart and as beautiful as you could love a monster like me.” Oswald blurted, dread settling over him.

Your entire body stilled, “Oswald… you’re not a monster!” Then his words sunk in properly, “You…. you love me?”

Oswald’s eyelashes fluttered, “Well yes…. I…. I thought it was obvious.” He blushed awkwardly, loosening his grip on your arms and rubbing his hands along them. “I’ve always adored you. But you’re too… well too perfect for someone like me.”

Your heart, already aching from the hurt of watching him destroy your ardent words of affection, broke even further. His confession tugged at you, and despite some misgivings you drew him to you, brushing your lips against his. Oswald buried his hands in your hair, deepening the kiss. “I’m so sorry.” He apologised over and over again, moving to kiss away the salty remains of your grievances.

Then he was pulling you back into the study, closing the door softly behind you. “So beautiful.” Oswald worshipped, drawing those clear blue eyes of his over your body. His gentle touches ignited a fire of want in you. “Oh Oswald..” You sighed, closing your eyes in bliss as he moved to kiss along your neck and down to the gentle curve of your collarbones. It was everything you’d ever imagined.

“Yes my dove?” Oswald murmured, nuzzling his nose into the crook of your neck, taking a deep breath of your perfume.

“I love you.”  
“And I, you.” Oswald affirmed, then distracted you into another collection of kisses. Lips brushing against each other, tongues teasing soft moans from each other while hands wandered. For all the misunderstandings, this was the perfect conclusion to such a heart wrenching day.


	4. Roses (mugging)

Oswald paused during his luncheon walk outside a flower shop. He eyed the roses with a bit of longing. “Boss, do you mind if I pick something up?” Gabe was beside him, “It’s my mom’s birthday today.”

Oswald waved a hand, “Of course, Gabe.” He gently touched the blossoms as Gabe went in to the shop to make his purchase. He sharply glanced up at a couple leaving the shop, adoration in their eyes when they smiled at each other, a single rose in hand. A pang of longing was felt in his chest. There were moment’s like these he wished he had someone to bestow beautiful flowers upon.

You were inside the shop, helping a large man in a leather jacket pick out a suitable bouquet of flowers. Your eyes caught a sad looking figure through the window. There was something about the morose looking man that drew you to him. Why did he look so forlorn? You imagined his smile would be brilliant.

“Excuse me… do you know who that man is?” You asked, passing the yellow roses to the customer who had introduced himself as Gabe.

Gabe glanced at where you gestured. “Oh that’s Mr. Cobblepot.”

You directed Gabe to the other shop girl to pay for his flowers. Grabbing a single white rose, you stepped outside. “Excuse me, Sir?”

Oswald glanced up at you crossly. “What?” He took in your appearance. A shop girl, in a t-shirt and jeans with a green apron tied over top.

“I just…. well I just wanted to give you this.” You held out the rose. He took it from you, rolling the stem between his fingers. “A man as handsome as you should smile more.” You complimented. He was handsome, in a irregular sort of way. Dark hair contrasted greatly against his skin and you could easily get lost in those crystalline blue eyes.

His mouth curled up in a sneer. “I don’t need your pity.” Oswald spat. You took a hasty step back. His eyes slid past you to Gabe, “We’re leaving.” He said shortly and turned on his heel to walk away. You studied his gait and then realized… This was the Penguin that people had been talking about. Feeling a bit faint and hurt at his reaction, you returned to the shop.

Oswald almost threw away the rose, but instead his gaze softened at the unexpected gift and he placed it carefully through his lapel buttonhole on his suit. It was stark and pure against the black fabric.

Later…

It was getting dark out, the fall months drained the daylight up so quickly. You’d already sent the other girl home, she had a longer walk then you did. You carefully locked up the shop and started your walk home, your ballcap low on your forehead and sweater tugged firmly around you. Best to be invisible, then maybe you wouldn’t get mugged.

Apparently you had no such luck.

Rough hands grabbed you and you fought back, struggling in their grasp. “Get off!” You swung your bag around, hitting them repeatedly. A backhand to your face made your nose bleed, while the punch to the stomach cause you to crumple and fall to the concrete .

A car swerved to the curb, and sharp black shoes hobbled past you. You glanced up blearily, as the owner of those shoes, beat the man with a wickedly sharp umbrella. Your assailant was a bloody mess when he was done. “Mr. Cobblepot?” You whispered.

“I’m here.” He soothed, kneedly awkwardly beside you. His gloved hands helped you up and he guided you to the backseat of his car. “Gabe…” Oswald gave his man a meaningful gaze. His men would take “care” of the man. Oswald shook his head. Assaulting nice civilians was no way to treat a lady.

“I’d like to take you to my home, if that’s alright?” He gently held your chin, studying the damage left.

Overcome, you burst into tears and he carefully gathered you into his arms. “Shh… it’s alright.”

You buried your face into his suit, sobs wracking your body. Oswald made soothing sounds and rubbed your back, hoping you’d relax. The scent of a rose caught your attention. Sniffling you leaned back and wiped at your eyes. “You kept the rose.”

Oswald had the decency to look embarrassed. “I’d like to formally apologise for my wretched behavior earlier today. I’m afraid that I don’t take compliments well. Especially from a beautiful girl.”

In disbelief, “You think I’m beautiful?” You asked, glancing away. He cleared his throat. “I meant what I said. You are beautiful.”

You blushed, and replied, “And I meant what I said. Mr. Cobblepot”

Oswald smiled, “I know that now. Please… call me Oswald.” His fingers tentatively crossed the space between you to slip his hand into yours. You smiled up at him and he returned it, eyes lighting up.

You were right, he should smile more.


	5. Socks (borrowing his clothes)

**Summary for the Chapter:**

> Prompt: you’re snooping in his drawers. But you really just have cold feet! And maybe a sweater kthx. There you are snuggled in his clothes. T

Oswald came in late, slumping onto the chair to remove his shoes, tiredly tugging off his jacket and leaning back to rub his temples against the oncoming headache he could feel building in his temples. Remaking Gotham was proving to be a daunting task. His head lifted at the sound of a soft grumbling sigh coming from the couch. 

You were curled up on the couch, wearing a oversized sweater, black shorts and socks. Oswald couldn’t quite put his finger on what was off about this picture. Then he realized when he slowly scanned down your body. He recognised the socks. They were a pair you had given him. One’s with little penguins. You’d bought them as a joke on his birthday.

Was that his…. sweater?

“Darling…” He sat down on the couch, moving your feet into his lap. “Mmm” You mumbled, slowly opening your eyes,

“Why are you wearing my clothes?” He’d also recognised the black silk boxers you wore. He had stuffed them in the back of his drawer. They felt too distracting to wear on a regular basis.  
You shrugged your shoulders, readjusting on the couch so you could look at him properly. His hands gently massaged your socked feet. “My feet were cold, and then I just decided to snoop through your closet. Plus it smells like you.”   
You said simply, tugging at the sweater. “I figured you wouldn’t miss these ones. I had no idea you had so many clothes. I had to dig all the way into the back to find this. Is this the only casual thing you own?” You questioned him with a raised eyebrow.

Oswald smiled, “I like suits.”

“I like them better when they’re on the floor.” You admitted.

“Is that so?” He smirked.


	6. Cookie Thief (Dadswald)

Oswald smiled warmly as he placed his palms against your swollen belly, he leaned in pressing a kiss to it. He was going to be a father.

“She’s going to be so beautiful. ” the words were spoken with reverence as he glanced up to you, slowly rising to kiss you. You hummed in response, enjoy the rare quiet moment between you.

….

She was beautiful. Oswald had never known love like that could exist until he saw his daughter for the first time. She was so small in his arms. A tuft of black hair and little rosebud lips. His heart swelled, kissing her brow softly. “Emilia Cobblepot, daddy will always be here for you.”

….

He witnessed her first steps. Those stumbling giggles that landed her straight into his arms as she laughed and wrapped her arms around his neck. Oswald peppered her face in kisses that had her bursting into giggles of joy before he sent her tottering back to you, his eyes alight in happiness.

…

He came home, looking forward to seeing his family. You were nestled on the couch, a novel in one hand, and the other absentmindedly stroking over the growing swell of your belly. Oswald was going to be a father again in a matter of months. He smiled at the thought, leaning over the couch to kiss your hair.

“Where’s Emilia?” he asked, a curious glance around the living room, surprised to not see his little dove anywhere.

You glanced up at him, your hand covering over his own on your shoulder. “She’s in the kitchen. I gave her a sandwich to finish.”

Oswald nodded, briefly squeezing your hand before letting go and meandering towards the kitchen.

Stepping in he frowned, a slight quirk to his lips as he spotted his daughter teetering on tiptoes to reach the top of the counter and thus the cookie jar. His daughter Emilia looked up at him as the door swung closed. She was just three, small and petite for her age with rounded cheeks and bright blue eyes.

“Emelia…” The tone was warning and immediately she dropped down from the counter, glancing guiltily at the cookie in hand before shoving it in her face.

“How many cookies have you had?” Oswald had a pretty good idea judging by the mostly empty jar and the crumbs covering his daughter’s sticky hands and face.

Chewing the cookie, she swallowed. “That was my last one.”

He had to admire the cheek she gave in such an evasive answer. “How many?”

Emelia shrugged, giving him a big innocent expression. “That was my last one, “ She repeated stubbornly.

Oswald sighed, “Emelia… this is the last time I will ask this. How many cookies have you had?”

She smiled widely at him. “Just this last one, daddy.” Her hands stretched up, small fingers wiggling as she demanded, “Up up.”

Oswald was terrible at saying no to her, but he did take note of the peanut butter smeared over her fingers and face. He sighed,“Let’s get you cleaned up, young lady.” 

Swinging her to sit on top of the counter, he reached for a cloth, dampening it with water before carefully holding her face and wiping away the traces of her snack, before moving onto her fingers. "There, now you’re presentable my little dove.”

He carefully put the remaining cookies away, now far out of her reach above the fridge. Though Oswald could already see her calculating look as she watched him move the jar. No doubt she would find a way into the cupboard later.

“She’s just like you…” Oswald and Emelia turned at the sound of your voice. You were standing in the doorway, watching the pair of them in amusement. Oswald chuckled. “Maybe that’s not such a bad thing.”

Especially growing up in a city like Gotham.


	7. My Everything (Ace Reader)

**Summary for the Chapter:**

> Prompt-I’m asexual and I’ve been dumped several times because I won’t “give out” and it just happened again… Could you do a fanfic with Oswald where the reader is scared he’ll leave them but then he assures them that he loves them for who they are and not sexual desires… (Anon)

It had happened before. There always seemed to be a tipping point. Where they wanted more than you could give. Rarely did it ever end well for you. They never understood your feelings, and so it would end. Even their claims of love fell apart when you explained who you were and how you felt.

In the end it all came down to one thing.

Sex.

It didn’t interest you in the slightest. It wasn’t a want or a need.

Being in a relationship with Oswald was remarkably easy at first. He was forever a gentleman, not even daring to hint at anything possibly… promiscuous as he once referred to a couple displaying excess public affection in the park once. Even alone together, your relationship had revolved around enjoyment of each other’s company, from deep conversations that lasted late into the night to the soft kisses and cuddling with hands entwined.

Tonight was different. Oswald had won the election and was the new Mayor of Gotham. So it was easy to celebrate with him. Drinks flowed and the excitement was there. You were so proud of him. Not just for winning, but for winning without the bribery. He was overjoyed at the results and it certainly came through when he gleefully cupped your face with his palms. Kisses were pressed to your cheeks and then finally against your soft lips.

“We did it! I won!”

“You did it Oswald!” You beamed at him.

He was flushed with excitement and even after the staff had left and Edward had retired leaving you two alone in his office, Oswald was still practically buzzing with elation. He took a seat in his plush leather wingback chair and lightly pulled you into his lap.

“I never thought this day would come! Mother would be so proud… I wish she’d known you… she would have loved you.” Oswald curved his palm to your cheek, drawing you down for a soft kiss. “I love you…” His eyes flickered between yours and then down to your lips before he pressed his own against yours.

Something changed. Whether it was the champagne or merely his lack of inhibitions this evening…His kisses were more passionate… more insistent, and his hands were wandering, sliding down your side and pushing up the hem of your shirt to caress the soft skin beneath. Immediately you were pulling away. This was dangerous territory that you didn’t want. It made you uncomfortable, especially when he didn’t notice your reluctance and continued kissing down the column of your throat. “Os….stop… I need to tell you something.”

Immediately he stopped, drawing back and watching you with confusion. There was a sharpness in his eyes…. Like he was partially expecting some terrible confession to spill from your lips. You supposed in some ways, he might consider it like that. But you had to tell him. Already you had avoided the discussion before, slipping out of any situation that got a little too close to needing to tell him.

“I…. Oswald… I’m asexual. It means I don’t have an interest in sex, and in my case… well it’s…. I don’t ever even want to have sex. I just… it’s me. It’s who I am, and it’s not going to change.” The words were hard to let go. This was always the moment where everything fell apart. But it had to happen eventually. “I know this will probably end things between us. It always has before. My last relationship… well they didn’t take it well in the slightest. Leaving is only inevitable.”

He appeared shocked, and it only caused your anxiety to worsen. You pulled away, slipping off his lap. Turning from him was hard as you wrapped your arms around yourself, preparing for the words you’d heard so many times before. That he didn’t understand. That he couldn’t have a relationship like this. That sex was necessary to it. That this would be the end and your fears of him leaving would come true.

Only they didn’t come. Instead you heard him stand, coming up behind you, his presence a warm shadow to your back.

“I can’t understand why someone would do that. Love is far more than sexual desires. My darling, my love for you is for who you are as a person.” Oswald’s voice was quiet, his hand gently reaching out and rubbing your back, “I respect and care for you. If such physical intimacy causes you distress, I understand entirely. It doesn’t change my love for you.”

Something within you broke at his words. Emotion overwhelmed and you bit your lip. He still loved you….Even knowing that you’d never want to be sexually intimate with him, he still loved you.

When you turned to look at him, he softened even more at the tears welling in your eyes. “Darling, come here.” His arms opened and you fell into them. Oswald held you close, stroking your hair and back reassuringly. “We will never do anything you don’t want to. I love you, my dove. I never ever want to hurt you. I want to be by your side, in any way that you will have me. You’re my everything.”

Burying your face against his chest, you smiled through the tears. He hadn’t left… he’d understood. Oswald had accepted you for exactly who you are.


End file.
